Experience Our Nautical Fleet in St. Michaels, Maryland

Experience Our Nautical Fleet in
St. Michaels, Maryland

Founded in 1819 by Navy man, seafarer, and hometown hero Samuel Hambleton, the nautical heritage of Perry Cabin runs deep — a fact that is reflected in our esteemed fleet.  The breadth and beauty of the fleet is a matter of pride and careful cultivation. From the timelessness of the historic Stanley Norman Skipjack to our modern, sleek motoring vessels and everything in between, we have something for every salty dog and landlubber alike.

A Fleet Built for the Chesapeake Bay and the Miles River

The breadth and beauty of the fleet at Inn at Perry Cabin is a matter of pride and careful cultivation. From the timelessness of the 1902 Stanley Norman Skipjack, one of the last working skipjacks remaining on the Chesapeake Bay, to sleek Alerion sailing yachts, a classic Friendship 40, and the custom Hinckley Talaria 55 flybridge motor yacht, every vessel has been chosen for its character and its ability to show guests what this stretch of the Eastern Shore looks like from the water. The fleet serves every type of guest. Solo travelers and couples can join captained group sailings alongside others on the Miles River. Families and private groups can book exclusive two-hour, half-day, or full-day private charters on sailing or motor vessels. And for those who want something beyond a standard cruise, guided excursions range from oyster dredging aboard the Stanley Norman to a 4-hour Chesapeake voyage past the Bay Bridge to Annapolis. There is something here for every first-time visitor and every guest who has been coming back to St. Michaels for years.

 

 

Sailing and Boating Experiences Unique to the Eastern Shore

What sets the Inn at Perry Cabin fleet apart is not just the quality of the vessels. It is the range of experiences only possible because of where the Inn sits. Depart from the Inn's private dock and you are on the Miles River in minutes, with the open Chesapeake Bay reachable by water without a car, a transfer, or a second reservation. The Skipjack Legacy Voyage takes guests aboard the 1902 Stanley Norman for a narrated historical sailing along the Miles River, connecting them to the oystering tradition that defined this region for generations. The Rum Running on the Skipjack experience pairs that same historic vessel with a curated Lyon Rum tasting on Wednesday evenings in summer, timed to coincide with the weekly sailboat races on the Miles River. The Explore the Chesapeake excursion boards the 55-foot Hinckley Five Star for a 4-hour voyage navigating past Kent Narrows, beneath the Chesapeake Bay Bridge, and into downtown Annapolis for a tour by water. Each of these experiences is bookable through the Inn's Guest Services team and is available to both overnight guests and day visitors seasonally.

A Waterfront Resort with a Dock at Your Door

Most resort sailing experiences require a trip to the marina. At Inn at Perry Cabin, the dock is part of the property. All charters and excursions depart from the Inn's private waterfront dock on the Miles River, giving guests direct access to the water from the moment they arrive. The Inn is located at 308 Watkins Lane in St. Michaels, Maryland, approximately 90 minutes from Washington D.C. and Baltimore. It holds a Forbes Four-Star rating and is a member of Historic Hotels of America, recognized for a nautical and cultural history that stretches back to 1815. Whether you are planning a romantic getaway, a family trip to the Eastern Shore, or a corporate retreat with something genuinely different on the agenda, the fleet at Inn at Perry Cabin gives every stay a reason to get out on the water.

Frequently Asked Questions

  • What sailing and boating experiences are available at Inn at Perry Cabin in St. Michaels?

    Inn at Perry Cabin offers a wide range of on-water experiences designed for both relaxation and adventure.

    • Private charters
    • Captained group sailings
    • Skipjack Legacy Voyage
    • Oyster Dredging Experience
    • Rum Running on the Skipjack with Lyon Rum
    • Wye Island kayak and paddleboard excursion
    • Explore the Chesapeake voyage to Annapolis

    All experiences depart from the Inn’s private dock on the Miles River and are available seasonally from April through October, with select experiences extending into November.

  • Do I need to be a hotel guest to join a sailing charter or excursion at Inn at Perry Cabin?

    No, you do not need to be a hotel guest for many experiences.

    Several excursions, including the Stanley Norman Skipjack voyages and the Wye Island experience, are open to day visitors as well as overnight guests.

    Private and group charters can be arranged through the Inn’s Guest Services team:

    Phone: 443.258.2228
    Email: [email protected]

  • What makes the nautical fleet at Inn at Perry Cabin historically significant?

    Inn at Perry Cabin has deep maritime roots dating back to 1815, when it was founded by Samuel Hambleton, a decorated Navy officer and hero of the Battle of Lake Erie.

    The fleet’s centerpiece is the 1902 Stanley Norman Skipjack, one of the last surviving vessels of its kind that once dredged oysters on the Chesapeake Bay. It is listed on the National Register of Historic Places.

    The Inn is also a proud member of Historic Hotels of America, recognized for preserving its rich maritime heritage.

  • Where is Inn at Perry Cabin located, and how far is it from Washington, D.C. and Baltimore?

    Inn at Perry Cabin is located at:

    308 Watkins Lane
    St. Michaels, MD 21663

    Set along the Miles River off the Chesapeake Bay, the Inn is easily accessible:

    • Approximately 90 minutes from Washington, D.C. via US-50 East across the Bay Bridge
    • Approximately 75 minutes from Baltimore

    Driving directions are available on the Inn’s contact page.

Related Content

Sailing the Chesapeake Bay from St. Michaels, Maryland

Some places are best discovered from the water. At Inn at Perry Cabin, the Chesapeake Bay and Miles River are not just a backdrop; they are the experience itself. Our fleet of sailing and motor vessels offers one of the most distinct ways to explore...

Read More

Meet Our Fleet in St. Michaels, Maryland

Founded in 1819 by Navy man, seafarer, and hometown hero Samuel Hambleton, the nautical heritage of Perry Cabin runs deep — a fact that is reflected in our esteemed fleet.


Read More

Sign Up for Ships Privileges

Subscribing is more than a newsletter; it’s access to exclusive offers and special promotions only available to subscribers. When you join, you become a member of the Crew and enjoy Ship’s Privileges reserved just for those INN the know!

Sign up now